CN112397664A

CN112397664A - Heterocyclic compound and organic light-emitting device comprising same

Info

Publication number: CN112397664A
Application number: CN202011089538.6A
Authority: CN
Inventors: 张焚在; 李东勋; 许东旭; 韩美连; 姜敏英
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2014-04-04
Filing date: 2015-04-02
Publication date: 2021-02-23
Also published as: CN106132937B; KR101737199B1; CN106164055B; TW201546052A; US10510963B2; US20170033294A1; KR20150115622A; KR20150115648A; CN106164055A; US20170018718A1; US10381572B2; TW201602087A; TWI542582B; US11877510B2; US10916710B2; CN106132937A; TWI548623B; KR20150115647A; KR101653920B1; US20190051839A1

Abstract

The present invention relates to a heterocyclic compound and an organic light-emitting device comprising the same. The present invention provides an organic light emitting device, comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed thereonBetween the first electrode and the second electrode, wherein one or more of the organic material layers comprises the structural formula:

and wherein the organic material layer containing the compound is an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons. The compound of the present invention can improve efficiency and improve low driving voltage and/or lifespan characteristics in an organic light emitting device.

Description

Heterocyclic compound and organic light-emitting device comprising same

This application is a divisional application filed on the filing date of 2015, 4/2, application No. 201580017744.7, entitled "heterocyclic compound and organic light emitting device comprising the same" (PCT/KR2015/003291, 2016, 9/29, national phase date).

The present invention claims the priority and benefit of korean patent application No. 10-2014-0040818, filed 4/2014 to the korean intellectual property office, korean patent application No. 10-2015-0017929, filed 5/2/2015 to the korean intellectual property office, and korean patent application No. 10-2015-0045586, filed 31/2015 3/10 to the korean intellectual property office, the entire contents of which are incorporated herein by reference.

Technical Field

The present invention relates to a heterocyclic compound and an organic light-emitting device comprising the same.

Background

In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy by using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer interposed therebetween. Herein, the organic material layer may have a multi-layer structure composed of different materials to improve efficiency and stability of the organic light emitting device in many cases, and for example, may be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between two electrodes, holes are injected from an anode into the organic material layer and electrons are injected from a cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to a ground state again.

There is a continuing need to develop new materials for the above-described organic light emitting devices.

Disclosure of Invention

Technical problem

The specification describes heterocyclic compounds and organic light emitting devices comprising the same.

Technical solution

Exemplary embodiments of the present invention provide compounds represented by the following formula 1:

[ formula 1]

In the formula 1, the first and second groups,

ar1 and Ar2 are the same as each other and are phenyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a heterocyclic group; biphenyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a; naphthyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a; or a phenanthryl, which is unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a,

l is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group,

r1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkyl (ene) sulfonyl; substituted or unsubstituted aryl (ene) thioacyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; substituted or unsubstituted heteroarylamino; substituted or unsubstituted arylamine; substituted or unsubstituted arylheteroarylamino; a substituted or unsubstituted aryl phosphine group; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or may form a substituted or unsubstituted ring together with an adjacent group,

r3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkyl (ene) sulfonyl; substituted or unsubstituted aryl (ene) thioacyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; a substituted or unsubstituted aryl phosphine group; or a substituted or unsubstituted phosphine oxide group; or may form a substituted or unsubstituted ring together with the adjacent groups,

m is an integer of 1 to 5,

a is an integer of 0 to3, and

b is an integer of 0 to 4, and

when m, a and b are respectively 2 or more, the structures in parentheses are the same as or different from each other.

Furthermore, an exemplary embodiment of the present invention provides: an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the compound of formula 1.

Advantageous effects

The compound described in this specification can be used as a material for an organic material layer of an organic light-emitting device. The compound according to at least one exemplary embodiment may improve efficiency and improve low driving voltage and/or lifespan characteristics in an organic light emitting device. In particular, the compounds described in the present specification can be used as a material for hole injection, hole transport, hole injection and hole transport, light emission, electron transport, or electron injection. Further, the compound described in the present specification can be preferably used as a material for a light-emitting layer, electron transport, or electron injection, and more preferably used as a material for electron transport or electron injection.

Drawings

Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

Fig. 2 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4.

Figure 3 illustrates the MS data results for compound 67 prepared in the examples.

Detailed Description

The present invention will be described in more detail hereinafter.

An exemplary embodiment of the present invention provides a compound represented by formula 1.

Examples of the substituent will be described below, but are not limited thereto.

In this specification, the term "substituted or unsubstituted" means that the group is unsubstituted or substituted with one or more substituents selected from: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; alkyl (ene) thioacyl; aryl (ene) thioacyl; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; and heterocyclyl, or substituents attached to two or more of the substituents exemplified above, substituted or unsubstituted. For example, "a substituent to which two or more substituents are attached" may be a biphenyl group. That is, the biphenyl group may also be an aryl group, and may be understood as a substituent with two phenyl groups attached.

According to an exemplary embodiment of the present invention, the term "substituted or unsubstituted" may preferably mean that the group is unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; an alkyl group; an alkoxy group; and an aryl group.

According to an exemplary embodiment of the present invention, the compound represented by formula 1 may be unsubstituted or substituted with at least one deuterium.

In the present specification, an "adjacent" group may refer to a substituent that replaces an atom directly bonded to an atom substituted with the corresponding substituent, a substituent that is disposed closest in space to the corresponding substituent, or another substituent that replaces an atom substituted with the corresponding substituent. For example, two substituents substituted at the ortho position of the phenyl ring, and two substituents substituted for the same carbon in the aliphatic ring, may be understood as groups "adjacent" to each other.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. In particular, the carbonyl group may be a compound having the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. In particular, the ester group may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. In particular, the imide group may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula-SiRR 'R ", and R, R' and R" may each be hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like.

In the present specification, the boron group may be represented by the formula-BRR 'R ", and R, R' and R" may each be hydrogen; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl. Specific examples of the boron group include a trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to still another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to still another exemplary embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples of the alkenyl group include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2-bis (diphenyl-1-yl) vinyl-1-yl,

phenyl, styryl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

In the present specification, specific examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group comprising the two or more aryl groups may comprise a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.

Specific examples of the arylamine group include, but are not limited to, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole, triphenylamine, and the like.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heterocyclic group or a polycyclic heterocyclic group. The heteroarylamine group comprising two or more heterocyclic groups may comprise a monocyclic heterocyclic group, a polycyclic heterocyclic group, or both a monocyclic heterocyclic group and a polycyclic heterocyclic group.

In the present specification, the arylheteroarylamino group means an amino group substituted with an aryl group and a heterocyclic group.

In the present specification, examples of the arylphosphino group include a substituted or unsubstituted monoarylphosphino group, a substituted or unsubstituted diarylphosphino group, or a substituted or unsubstituted triarylphosphino group. The aryl group in the aryl phosphine group may be a monocyclic aryl group or a polycyclic aryl group. The arylphosphino group comprising two or more aryl groups may comprise a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic aryl group and a polycyclic aryl group.

In the present specification, examples of the arylamine group refer to a substituted or unsubstituted monocyclic diarylamine group, a substituted or unsubstituted polycyclic diarylamine group, or substituted or unsubstituted monocyclic and polycyclic diarylamine groups.

In the present specification, the aromatic hydrocarbonThe group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to exemplary embodiments, the number of carbon atoms of the aryl group is 6 to 20. When the aryl group is a monocyclic aryl group, examples of the monocyclic aryl group include phenyl, biphenyl, terphenyl, and the like, but are not limited thereto. Examples of the polycyclic aromatic group include naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, perylene, etc,

A fluorenyl group, a biphenylylene group, etc., but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro ring structure.

When the fluorenyl group is substituted, the fluorenyl group can be

And the like. However, the fluorenyl group is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms thereof is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoxazolyl, oxadiazolyl (oxadiazolyl group), thiadiazolyl (thiadiazolyl group), benzothiazolyl, phenothiazinyl, dibenzofuranyl and the like, but are not limited thereto.

In the present specification, the description of the above heterocyclic group may be applied to a heteroaryl group other than an aromatic group.

In the present specification, the description of the above aryl group can be applied to aryl groups of aryloxy, arylthio, aryl (ene) thioacyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino and arylheteroarylamino groups.

In the present specification, the description of the above alkyl group can be applied to alkyl groups of alkylthio, alkyl (ene) sulfonyl, aralkyl, aralkylamino, alkylaryl and alkylamino groups.

In the present specification, the description of the above heterocyclic group can be applied to heteroaryl groups of heteroaryl groups, heteroarylamino groups and arylheteroarylamino groups.

In the present specification, the description of the above alkenyl group can be applied to an alkenyl group of an aralkenyl group.

In the present specification, the description of the above aryl group may be applied to an arylene group other than a divalent arylene group.

In the present specification, the description of the above heterocyclic group may be applied to a heteroarylene group other than a divalent heteroarylene group.

In the present specification, the meaning of forming a ring together with an adjacent group means forming a substituted or unsubstituted aliphatic hydrocarbon ring together with an adjacent group; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; substituted or unsubstituted aromatic heterocycle; and fused rings thereof.

In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon atoms and hydrogen atoms, which is a ring other than an aromatic group.

In the present specification, examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl, naphthyl, anthracenyl, and the like.

In the present specification, the aliphatic heterocyclic ring refers to an aliphatic ring containing one or more heteroatoms.

In the present specification, the aromatic heterocyclic ring refers to an aromatic ring containing one or more heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocyclic ring and the aromatic heterocyclic ring may be monocyclic or polycyclic.

According to an exemplary embodiment of the present invention, formula 1 may be represented by any one of the following formulae 2 to 4.

[ formula 2]

[ formula 3]

[ formula 4]

In the formulae 2 to 4, the reaction mixture,

ar1, Ar2, L, R3, R4, a, b and m are as defined in formula 1,

r11, R12, R21 and R22 have the same meanings as those of R3 and R4,

x1 and X2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkyl (ene) sulfonyl; substituted or unsubstituted aryl (ene) thioacyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; substituted or unsubstituted heteroarylamino; substituted or unsubstituted arylamine; substituted or unsubstituted arylheteroarylamino; a substituted or unsubstituted aryl phosphine group; or a substituted or unsubstituted phosphine oxide group; or may form a substituted or unsubstituted ring together with the adjacent groups,

r11 and r12 are the same as or different from each other and each independently an integer of 0 to 5,

r21 and r22 are the same as or different from each other and each independently an integer of 0 to 4, and

when r11, r12, r21 and r22 are each 2 or more, the structures in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present invention, formula 1 may be represented by any one of the following formulae 5 to 8.

[ formula 5]

[ formula 6]

[ formula 7]

[ formula 8]

In the case of the formulas 5 to 8,

ar1, Ar2, L, R1 to R4, m, a and b are as defined in formula 1.

According to an exemplary embodiment of the present invention, formula 2 may be represented by any one of the following formulae 2-1 to 2-4.

[ formula 2-1]

[ formula 2-2]

[ formulas 2 to 3]

[ formulae 2 to 4]

In formulae 2-1 to 2-4,

ar1, Ar2, L, R3, R4, a and b are as defined in formula 1,

r11, R12, R11 and R12 are as defined in formula 2.

According to an exemplary embodiment of the present invention, formula 3 may be represented by any one of the following formulae 3-1 to 3-4.

[ formula 3-1]

[ formula 3-2]

[ formula 3-3]

[ formulas 3 to 4]

In formulae 3-1 to 3-4,

ar1, Ar2, L, R3, R4, a and b are as defined in formula 1, and

r21, R22, R21 and R22 are as defined in formula 3.

According to an exemplary embodiment of the present invention, X1 and X2 are the same or different from each other and each is independently a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the invention, X1 and X2 are the same or different from each other and each is independently an alkyl group.

According to an exemplary embodiment of the invention, X1 and X2 are methyl.

According to an exemplary embodiment of the invention, Ar1 and Ar2 are the same as each other and are phenyl, unsubstituted or substituted with one or more substituents selected from deuterium and alkyl; biphenyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl; naphthyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, and aryl; or phenanthryl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl.

According to an exemplary embodiment of the invention, Ar1 and Ar2 are the same as each other and are phenyl, unsubstituted or substituted with deuterium; biphenyl, unsubstituted or substituted with deuterium; naphthyl, unsubstituted or substituted with deuterium; or phenanthryl, unsubstituted or substituted with deuterium.

According to an exemplary embodiment of the invention, Ar1 and Ar2 are identical to each other and are phenyl, biphenyl, naphthyl or phenanthryl.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; alkyl (ene) thioacyl; aryl (ene) thioacyl; an alkenyl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an arylheteroarylamino group; an aryl phosphine group; a phosphine oxide group; aryl, unsubstituted or substituted with deuterium, alkyl or alkoxy; or a heterocyclic group, or may form a ring together with an adjacent group.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted alkyl; or substituted or unsubstituted aryl groups, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; alkyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a; or aryl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a heterocyclic group, or combine with each other to form a ring which is unsubstituted or substituted with one or more substituents: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; alkyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, alkoxy and aryl; or an aryl group, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, alkoxy and aryl, or combined with each other to form a ring, said ring being unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, alkoxy and aryl.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently hydrogen; an alkyl group; or aryl, unsubstituted or substituted with one or more substituents selected from deuterium, a halogen group, an alkyl group and an alkoxy group, or combined with each other to form a ring.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group; or substituted or unsubstituted monocyclic to tricyclic aryl groups, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group; or substituted or unsubstituted phenyl groups, or combine with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present invention, R1 and R2 are the same as or different from each other, and each is independently hydrogen, deuterium, a halogen group, an alkyl group, and an aryl group, or combine with each other to form a ring.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently an alkyl group; and an aryl group, or combine with each other to form a ring.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently an alkyl group; or phenyl groups, or combine with each other to form a ring.

According to an exemplary embodiment of the invention, R1 and R2 are the same or different from each other and are each independently methyl; or phenyl groups, or combine with each other to form a ring.

According to an exemplary embodiment of the invention, R3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; alkyl (ene) thioacyl; aryl (ene) thioacyl; an alkenyl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; an aryl phosphine group; or a phosphine oxide group.

According to an exemplary embodiment of the invention, R3 and R4 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group or an alkyl group.

According to an exemplary embodiment of the invention, R3 and R4 are hydrogen.

According to an exemplary embodiment of the invention, R4 is hydrogen.

According to an exemplary embodiment of the invention, R3 is hydrogen.

According to an exemplary embodiment of the invention, L is phenylene, unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a; or biphenylene, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a.

According to an exemplary embodiment of the invention, L is phenylene; or biphenylene.

According to an exemplary embodiment of the present invention, L may be any one selected from the following structures.

The structure may be unsubstituted or substituted with one or more substituents selected from: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; alkyl (ene) thioacyl; aryl (ene) thioacyl; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; and heterocyclic groups.

According to an exemplary embodiment of the invention, the

May be any one selected from the following structures.

In the above-described structure, the first and second electrodes are formed on the substrate,

r1 and R2 are as defined in formula 1, and

According to an exemplary embodiment of the invention, m is 1.

According to an exemplary embodiment of the invention, m is 1 or 2.

According to an exemplary embodiment of the present invention, the compound of formula 1 may be any one selected from the group consisting of:

the compound represented by formula 1 can be prepared based on the preparation examples to be described below. According to one exemplary embodiment, the compound may be prepared, for example, by the following reaction scheme 1.

[ reaction formula 1]

In the reaction scheme 1, the reaction is carried out,

ar1, Ar2, L, R1, R2, R3, R4, a, b and m are as defined in formula 1.

In particular, according to an exemplary embodiment of the present invention, the compound of formula 1 may be prepared by coupling a compound of a halogen-substituted triazine derivative with an aromatic compound substituted with boric acid or a boric acid derivative using a palladium-catalyzed reaction.

Also, the present invention provides an organic light emitting device comprising the compound represented by any one of formula 1 to formula 8.

An exemplary embodiment of the present invention provides an organic light emitting device, including: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers include the compound of any one of formulas 1 to 8.

The organic material layer of the organic light emitting device of the present invention may also be composed of a single layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.

In one exemplary embodiment of the present invention, the organic material layer comprises a hole injection layer, a hole transport layer, or a layer simultaneously transporting and injecting holes, and the hole injection layer, the hole transport layer, or the layer simultaneously transporting and injecting holes comprises the compound of formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of formula 1.

According to an exemplary embodiment of the present invention, the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound of any one of formulas 1 to 8.

In an exemplary embodiment of the present invention, the electron transport layer, the electron injection layer, or the layer simultaneously transporting and injecting electrons comprises the compound of formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer includes a compound of any one of formulas 1 to 8.

In still another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In still another exemplary embodiment, the organic light emitting device may be an organic light emitting device having an inverted structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to an exemplary embodiment of the present invention is illustrated in fig. 1 and 2.

Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the structure, the compound may be included in the light-emitting layer.

Fig. 2 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4. In the structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic light emitting device of the present invention may be manufactured by materials and methods known in the art, except that one or more of the organic material layers include the compound of the present invention, i.e., the compound of any one of formulas 1 to 8.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

An exemplary embodiment of the present invention is an organic light emitting device comprising: a first electrode; a second electrode disposed to face the first electrode; a light emitting layer disposed between the first electrode and the second electrode; and two or more organic material layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound. In one exemplary embodiment, as the two or more organic material layers, two or more may be selected from an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects electrons, and a hole blocking layer.

In one exemplary embodiment of the present invention, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound. In particular, in one exemplary embodiment of the present invention, the heterocyclic compound may be further included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in one exemplary embodiment of the present invention, when the heterocyclic compound is included in each of the two or more electron transport layers, other materials than the heterocyclic compound may be the same as or different from each other.

The organic light emitting device of the present invention may be manufactured by materials and methods known in the art, except that one or more of the organic material layers include the compound of any one of formulas 1 to 8, i.e., the compound represented by any one of formulas 1 to 8.

For example, the organic light emitting device of the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light emitting device may be manufactured by: an anode is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate using a Physical Vapor Deposition (PVD) method such as sputtering or electron beam evaporation, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to the above-described methods, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

Further, when manufacturing an organic light emitting device, the compound of any one of formulas 1 to 8 may be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Herein, the solution application method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to the above-described methods, an organic light emitting device may be manufactured by sequentially stacking a cathode material, an organic material layer, and an anode material on a substrate (international publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In an exemplary embodiment of the invention, the first electrode is an anode and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is generally preferable in order to smoothly inject holes into the organic material layer. Specific examples of the anode material that can be used in the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals with oxides, e.g. ZnO: Al or SnO₂Sb; conducting polymers, e.g. poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.

As the cathode material, a material having a small work function is generally preferable in order to smoothly inject electrons into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; materials of multi-layer construction, e.g. LiF/Al or LiO₂Al, etc., but are not limited thereto.

The hole injection material is a layer that injects holes from an electrode, and is preferably a compound having an ability to transport holes, and thus has a role of injecting holes at an anode and an excellent role of injecting holes for a light emitting layer or a light emitting material, prevents excitons generated from the light emitting layer from moving to the electron injection layer or the electron injection material, and is excellent in forming a thin film. Preferably, the Highest Occupied Molecular Orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine organic materials, hexanenitrile hexaazabenzophenanthrene organic materials, quinacridone organic materials, perylene organic materials, anthraquinone, polyaniline, polythiophene-based conductive polymer, and the like, but are not limited thereto.

The electron transport material is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and the hole transport material is suitably a material that can receive holes from the anode or the hole injection layer to transfer the holes to the light emitting layer, and has a large hole mobility. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, block copolymers in which a conjugated portion and a non-conjugated portion are present together, and the like.

The light emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine the holes and the electrons to emit light in a visible ray region, and is preferably a material having excellent quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq 3); carbazole-based compounds; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benzimidazole compounds; poly (p-styrene) (PPV) based polymers; a spiro compound; polyfluorene, rubrene (lubrene), and the like, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocyclic ring-containing compounds and the like. Specifically, examples of the condensed aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but examples thereof are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. In particular, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine groupAnd examples thereof include pyrene having arylamine group, anthracene,

Diindenopyrene, and the like, and the styrylamine compound is a compound in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group and one or two or more substituents selected from aryl, silyl, alkyl, and cycloalkyl, and an arylamine group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styrenediamine, styrenetriamine, styrenetetramine, and the like. Further, examples of the metal complex include iridium complexes, platinum complexes, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and the electron transport material is a material that can well receive electrons from the cathode and transport the electrons to the light emitting layer, and is suitably a material having a large electron mobility. Specific examples thereof include: al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; and hydroxyflavone-metal complexes, but are not limited thereto. The electron transport layer may be used with any desired cathode material, such as according to the related art. Examples of suitable cathode materials are, in particular, conventional materials with a low work function, followed by an aluminum or silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound having an ability to transport electrons, has an effect of injecting electrons from a cathode and an excellent effect of injecting electrons into a light emitting layer or a light emitting material, prevents excitons generated from the light emitting layer from moving to a hole injection layer, and is excellent in forming a thin film. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and its derivatives, metal complexes, nitrogen-containing five-membered derivatives, and the like, but are not limited thereto.

Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), gallium tris (8-quinolinolato), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), chlorogallium bis (2-methyl-8-quinolinolato), gallium bis (2-methyl-8-quinolino) (o-cresol), aluminum bis (2-methyl-8-quinolino) (1-naphthol), gallium bis (2-methyl-8-quinolino) (2-naphthol), and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

In one exemplary embodiment of the present invention, the compound of formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Modes for carrying out the invention

The preparation of the compound represented by formula 1 and the organic light emitting device comprising the same will be specifically described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.

< preparation example >

< preparation example 1> preparation of Compound 1>

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (2- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-ane (19.4g, 37.4mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 1](19.9g, yield 85%, MS: [ M + H ]]⁺＝626)。

< preparation example 2> preparation of [ Compound 2]

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (4- (9,9' -spirobi [ fluorene)]-2-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (19)4g, 37.4mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 2]](18.7g, yield 80%, MS: [ M + H ]]⁺＝624)。

< preparation example 3> preparation of [ Compound 3]

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (7- (9, 9-diphenyl-9H-fluoren-4-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-ane (19.4g, 37.4mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 3](18.0g, yield 77%, MS: [ M + H ]]⁺＝626)。

< preparation example 4> preparation of [ Compound 5]

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (3- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (19.4g, 37.4mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8gPd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 5]]. (16.9g, yield 72%, MS: [ M + H ]]⁺＝626)

< preparation example 5> preparation of [ Compound 7]

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (2- (9, 9-diphenyl-9H-fluoren-2-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan-ane (19.4g, 37.4mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8gPd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 7]]. (17.8g, yield 76%, MS: [ M + H ]]⁺＝626)

< preparation example 6> preparation of [ Compound 13]

2, 4-di ([1, 1' -biphenyl) is added]-4-yl) -6-chloro-1, 3, 5-triazine (10.0g, 23.8mmol) and 2- (4- (9, 9-dimethyl-9H-fluoren-2-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (9.4g, 23.8mmol) were placed in 100ml THF. 50ml of 2.0M K was put therein₂CO₃And 0.5g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby producing [ compound 13]. (12.3g, yield 79%, MS: [ M + H ]]⁺＝654)

< preparation example 7> preparation of [ Compound 27]

2-chloro-4, 6-bis (naphthalen-1-yl) -1,3, 5-triazine (10.0g, 27.2mmol) and 2- (4- (9, 9-diphenyl-9H-fluoren-4-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (14.7g, 27.2mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.6g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 27]]. (13.8g, yield 70%, MS: [ M + H ]]⁺＝726)

< preparation example 8> preparation of [ Compound 32]

2-chloro-4, 6-di (naphthalen-2-yl) -1,3, 5-triazine (10.0g, 27.2mmol) and 2- (4- (9,9' -spirobi [ fluorene)]-4-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (14.1g, 27.2mmol) is taken in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.6g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 7 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 32]]。(15.0g，Yield 76%, MS: [ M + H ]]⁺＝724)

< preparation example 9> preparation of [ Compound 36]

2-chloro-4, 6-bis (phenanthren-9-yl) -1,3, 5-triazine (10.0g, 21.4mmol) and 2- (4- (9, 9-dimethyl-9H-fluoren-1-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (8.5g, 21.4mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.5g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 5 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 36]]. (11.6g, yield 77%, MS: [ M + H ]]⁺＝702)

< preparation example 10> preparation of Compound 46 >

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (4'- (9, 9-diphenyl-9H-fluoren-2-yl) - [1,1' -biphenyl ] are mixed]-4-yl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (22.3g, 37.4mmol) in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 6 hours.

The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 46]]. (17.9g, yield 68%, MS: [ M + H ]]⁺＝702)

< preparation example 11> preparation of Compound 47 >

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (4'- (9,9' -spirobi [ fluorene)]-2-yl) - [1,1' -biphenyl]-4-yl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (22.2g, 37.4mmol) in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 47]. (21.2g, yield 81%, MS: [ M + H ]]⁺＝700)

< preparation example 12> preparation of [ Compound 67]

2-chloro-4, 6-diphenyl-1, 3, 5-triazine (10.0g, 37.4mmol) and 2- (4'- (9, 9-diphenyl-9H-fluoren-4-yl) - [1,1' -biphenyl ] are mixed]-4-yl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (22.3g, 37.4mmol) in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 8 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 67]]. (18.6g, yield 71%, MS: [ M + H ]]⁺＝702)

< preparation example 13> preparation of Compound 80 >

2-chloro-4, 6-bis (phenyl-d 5) -1,3, 5-triazine (10.0g, 36.0mmol) and 2- (4- (9, 9-diphenyl-9H-fluoren-4-yl) phenyl) -4,4,5, 5-tetramethyl-1, 3, 2-dioxaborolan (18.7g, 36.0mmol) were placed in 150ml THF. 75ml of 2.0M K was put therein₂CO₃And 0.8g Pd (PPh)₃)₄The resulting mixture was then stirred and refluxed for 6 hours. The mixture was cooled to normal temperature, and then a solid produced by filtering the mixture was recrystallized with chloroform and ethanol, thereby preparing [ compound 80]]. (16.0g, yield 70%, MS: [ M + H ]]⁺＝636)

< example >

[ example 1]

Coating Indium Tin Oxide (ITO) to have a thin layer

The glass substrate of the thickness was put in distilled water in which a cleaning agent was dissolved, and ultrasonic cleaning was performed. In this case, a product manufactured by Fischer co. was used as a detergent, and distilled water filtered twice using a filter manufactured by Millipore co. was used as the distilled water. After washing the ITO for 30 minutes, two ultrasonic washes were performed for 10 minutes using distilled water. After the washing with distilled water was completed, ultrasonic washing was performed using isopropyl alcohol, acetone, and methanol solvents, and drying was performed, and then the product was transferred to a plasma washer. In addition, the baseThe bottom was purged with oxygen plasma for 5 minutes and then transferred to a vacuum evaporator.

The following compound [ HI-A]Thermal vacuum deposition onto a transparent ITO electrode prepared as described above

Thereby forming a hole injection layer. The compound [ HAT]

And the following compound [ HT-A]

Sequentially vacuum-depositing on the hole injection layer to form a hole transport layer.

Subsequently, the following compound [ BH]And compound [ BD]Vacuum depositing on the hole transport layer at a weight ratio of 25:1 to a layer having

Thereby forming a light emitting layer.

Will [ compound 1]And the following compound [ LiQ](quinoline lithium) was vacuum-deposited on the light emitting layer at a weight ratio of 1:1, thereby forming a light emitting diode having

Electron injection and transport layer of thickness (v). Lithium fluoride (LiF) and aluminum are then deposited on the electron injection and transport layers to have a layer of each

And

thereby forming a cathode.

In the above step, the deposition rate of the organic material is maintained at

Deposition rates of lithium fluoride and aluminum of the cathodeThe rates are respectively maintained at

And

and the degree of vacuum during deposition was maintained at 1X 10^-7Hold in the palm to 5 x 10^-8And supporting to thereby manufacture an organic light emitting device.

[ example 2]

An organic light-emitting device was produced in the same manner as in [ example 1] except that [ compound 2] was used instead of [ compound 1] of [ example 1 ].

[ example 3]

An organic light-emitting device was produced in the same manner as in [ example 1] except that [ compound 3] was used instead of [ compound 1] of [ example 1 ].

[ example 4]

An organic light-emitting device was produced in the same manner as in [ example 1] except that [ compound 5] was used instead of [ compound 1] of [ example 1 ].

[ example 5]

An organic light-emitting device was produced in the same manner as in [ example 1] except that [ compound 7] was used instead of [ compound 1] of [ example 1 ].

[ example 6]

An organic light-emitting device was manufactured in the same manner as [ example 1] except that [ compound 13] was used instead of [ compound 1] of [ example 1 ].

[ example 7]

An organic light-emitting device was manufactured in the same manner as in [ example 1] except that [ compound 27] was used instead of [ compound 1] of [ example 1 ].

[ example 8]

An organic light-emitting device was manufactured in the same manner as [ example 1] except that [ compound 32] was used instead of [ compound 1] of [ example 1 ].

[ example 9]

An organic light-emitting device was produced in the same manner as in [ example 1] except that [ compound 36] was used instead of [ compound 1] of [ example 1 ].

[ example 10]

An organic light-emitting device was manufactured in the same manner as [ example 1] except that [ compound 46] was used instead of [ compound 1] of [ example 1 ].

[ example 11]

An organic light-emitting device was manufactured in the same manner as [ example 1] except that [ compound 47] was used instead of [ compound 1] of [ example 1 ].

[ example 12]

An organic light-emitting device was manufactured in the same manner as [ example 1] except that [ compound 67] was used instead of [ compound 1] of [ example 1 ].

[ example 13]

An organic light-emitting device was manufactured in the same manner as [ example 1] except that [ compound 80] was used instead of [ compound 1] of [ example 1 ].

Comparative example 1

An organic light-emitting device was produced in the same manner as in [ mutexample 1] mutexcept that [ ET-a ] was used instead of [ compound 1] of [ mutexample 1 ].

Comparative example 2

An organic light-emitting device was produced in the same manner as in [ example 1] except that [ ET-B ] was used instead of [ compound 1] of [ example 1 ].

For the organic light emitting device manufactured by the above method, at 10mA/cm²The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm²Measuring the time (T) to reach a value of 90% compared to the initial brightness at a current density of (2)₉₀). The results are shown in table 1 below.

[ Table 1]

According to the results of the table, the compound represented by formula 1 according to the present invention may be used in an organic layer of the organic light emitting device that can simultaneously inject and transport electrons. An organic light emitting device using the same has a low driving voltage and high efficiency, and the stability of a device can be improved by the hole stability of the compound.

In particular, the compound represented by formula 1 according to the present invention is excellent in thermal stability and can be used in a mixture with an n-type dopant when used in an organic layer for simultaneously injecting and transporting electrons.

Further, according to an exemplary embodiment of the present invention, the case where the compound represented by formula 8 is used for an organic light emitting device has a lower driving voltage and/or higher efficiency, and the stability of the device may be increased due to hole stability of the compound, as compared to the case where the compound represented by formula 5 to formula 7 is used for an organic light emitting device.

[ description of reference numerals ]

1: substrate

2: anode

3: luminescent layer

4: cathode electrode

5: hole injection layer

6: hole transport layer

7: luminescent layer

8: electron transport layer

The invention also provides the following technical scheme:

note 1. A compound represented by the following formula 1:

[ formula 1]

In the formula 1, the first and second groups,

ar1 and Ar2 are the same as each other and are phenyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a heterocyclic group; biphenyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a; naphthyl, unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a; or a phenanthryl, which is unsubstituted or substituted with one or more substituents selected from: deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkyl (ene) sulfuryl group, an aryl (ene) sulfuryl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphine group, and a;

l is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

r1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkyl (ene) sulfonyl; substituted or unsubstituted aryl (ene) thioacyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; substituted or unsubstituted heteroarylamino; substituted or unsubstituted arylamine; substituted or unsubstituted arylheteroarylamino; a substituted or unsubstituted aryl phosphine group; a substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl; or a substituted or unsubstituted heterocyclic group, or optionally together with adjacent groups form a substituted or unsubstituted ring,

r3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkyl (ene) sulfonyl; substituted or unsubstituted aryl (ene) thioacyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; a substituted or unsubstituted aryl phosphine group; or a substituted or unsubstituted phosphine oxide group; or optionally together with adjacent groups form a substituted or unsubstituted ring,

m is an integer of 1 to 5,

a is an integer of 0 to3, and

b is an integer of 0 to 4, and

when m, a and b are each 2 or more, the structures in parentheses are the same as or different from each other.

Note 2. the compound according to note 1, wherein formula 1 is represented by any one of the following formulae 2 to 4:

[ formula 2]

[ formula 3]

[ formula 4]

In the formulae 2 to 4, the reaction mixture,

ar1, Ar2, L, R3, R4, a, b and m are as defined in formula 1,

r11, R12, R21 and R22 have the same meanings as those of R3 and R4,

x1 and X2 are the same or different from each other and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; substituted or unsubstituted silyl; a substituted or unsubstituted boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted arylthio; substituted or unsubstituted alkyl (ene) sulfonyl; substituted or unsubstituted aryl (ene) thioacyl; substituted or unsubstituted alkenyl; substituted or unsubstituted aralkyl; substituted or unsubstituted aralkenyl; substituted or unsubstituted alkylaryl; substituted or unsubstituted alkylamino; a substituted or unsubstituted aralkylamino group; substituted or unsubstituted heteroarylamino; substituted or unsubstituted arylamine; substituted or unsubstituted arylheteroarylamino; a substituted or unsubstituted aryl phosphine group; or a substituted or unsubstituted phosphine oxide group; or optionally together with adjacent groups form a substituted or unsubstituted ring,

when r11, r12, r21, and r22 are each 2 or more, the structures in parentheses are the same as or different from each other.

Note 3. the compound according to note 1, wherein formula 1 is represented by any one of the following formulae 5 to 8:

[ formula 5]

[ formula 6]

[ formula 7]

[ formula 8]

In the case of the formulas 5 to 8,

ar1, Ar2, L, R1 to R4, m, a and b are as defined in formula 1.

Appendix 4. the compound according to appendix 1, wherein L is any one selected from the following structures:

the structure is optionally unsubstituted or substituted with one or more substituents selected from: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; alkyl (ene) thioacyl; aryl (ene) thioacyl; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; and heterocyclic groups.

Note 5. the compound according to note 1, wherein L is phenylene or biphenylene.

Note 6. the compound according to note 1, wherein Ar1 and Ar2 are the same as each other, and are phenyl which is unsubstituted or substituted with one or more substituents selected from deuterium and alkyl; biphenyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl; naphthyl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl, and aryl; or phenanthryl, unsubstituted or substituted with one or more substituents selected from deuterium, alkyl and aryl.

Note 7. the compound according to note 1, wherein R1 and R2 are the same as or different from each other, and each independently is an alkyl group; or aryl, unsubstituted or substituted with one or more substituents selected from deuterium, a halogen group, alkyl and alkoxy; or combine with each other to form a ring.

Note 8. the compound according to note 1, wherein R3 and R4 are hydrogen.

Appendix 9. the compound according to appendix 1, wherein

The moiety is any one selected from the following structures:

r1 and R2 are as defined in formula 1, and

the structure can be unsubstituted or substituted with one or more substituents selected from: deuterium; a halogen group; a nitrile group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; an arylthio group; alkyl (ene) thioacyl; aryl (ene) thioacyl; a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; and heterocyclic groups.

Note 10. the compound according to note 1, wherein the compound of formula 1 is any one selected from the group consisting of:

note 11 that an organic light-emitting device includes:

a first electrode;

a second electrode disposed to face the first electrode; and

one or more layers of organic material disposed between the first electrode and the second electrode,

wherein one or more of the organic material layers comprise the compound according to any one of notes 1 to 10.

Note 12 the organic light-emitting device according to note 11, wherein the organic material layer containing the compound is a hole injecting layer, a hole transporting layer, or a layer that injects and transports holes at the same time.

Note 13 the organic light-emitting device according to note 11, wherein the organic material layer containing the compound is an electron injecting layer, an electron transporting layer, or a layer that injects and transports electrons at the same time.

Note 14 that the organic light-emitting device according to note 11, wherein the organic material layer containing the compound is a light-emitting layer.

Claims

1. An organic light emitting device comprising:

a first electrode;

a second electrode disposed to face the first electrode; and

wherein one or more of the organic material layers comprise a compound represented by the following formula 6, and

wherein the organic material layer containing the compound is an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons:

[ formula 6]

In the case of the formula 6, the,

ar1 and Ar2 are the same as each other and are phenyl, biphenyl, or naphthyl, which are unsubstituted or substituted with one or more substituents selected from deuterium and an alkyl group having 1 to 20 carbon atoms;

l is phenylene which is substituted or unsubstituted with one or more substituents selected from deuterium and an alkyl group having 1 to 20 carbon atoms, or biphenylene which is substituted or unsubstituted with one or more substituents selected from deuterium and an alkyl group having 1 to 20 carbon atoms,

r1 and R2 are the same as or different from each other, and are each independently an alkyl group having 1 to 20 carbon atoms which is unsubstituted or substituted with one or more substituents selected from deuterium, an alkyl group having 1 to 20 carbon atoms, and an aryl group having 6 to30 carbon atoms,

r3 and R4 are the same or different from each other and are each independently hydrogen; deuterium; or an alkyl group having 1 to 20 carbon atoms,

m is an integer of 1 to 5,

a is an integer of 0 to3, and

b is an integer of 0 to 4, and

2. An organic light-emitting device according to claim 1 wherein L is any one selected from the following structures:

the structure is optionally unsubstituted or substituted with one or more substituents selected from: deuterium; and an alkyl group having 1 to 20 carbon atoms.

3. An organic light-emitting device according to claim 1 wherein L is phenylene or biphenylene.

4. The organic light-emitting device according to claim 1, wherein R1 and R2 are the same as or different from each other and are each independently an alkyl group having 1 to 20 carbon atoms.

5. The organic light emitting device of claim 1, wherein R3 and R4 are hydrogen.

6. The organic light emitting device of claim 1, wherein the compound of formula 6 is any one selected from the group consisting of:

[ Compound 45]

[ Compound 48]

7. The organic light emitting device of claim 1, wherein R3 and R4 are methyl.

8. The organic light-emitting device of claim 1, wherein Ar1 and Ar2 are the same as each other and are phenyl, biphenyl, or naphthyl.